The number one question I’ve received since opening Ann Leonard Photography is “What should I wear?” The truth is that there isn’t a single right answer to this question. It depends on the type of session, the season, and a lot about you.
However, in the effort to create a place for you to start perusing the right section of your closet, or give you a great excuse for a mini-shopping spree, I present my Fall 2019 guide of “5 Things to Wear for a Fall Photo Session”.
1. Do Yourself a Solid

Do you see these two killing it in their best formal wear? I know this is from a summer shoot, but let me tell you what I love: the solid clothing that shows off these two personalities without stealing the image. Remember that the purpose of a portrait session is to showcase YOU and not your clothes. Prints tend to distract from faces, and showcase the clothing rather than the people. I want to tell your story and not the story of your clothes, so I always recommend solids as a first choice to clients.
2. Color Me Beautiful

What color solids you ask? Well, apparently this is quite the controversial subject. A lot of photographers out there prefer the clean crispness of neutral shades. To the credit of neutrals, they do photograph fabulously. However, for fall, I am a sucker for the warm shades of falling leaves, crisp apples, and golden sunsets.
Check out these Pintrest color boards for some great ideas of warm colors (warm neutrals get extra brownie points) as a springboard for your shopping list.
3. Coordination Is Key

What I love about those Pintrest colors up above is that they’re grouped together to aid in the coordinating of outfits. Matchy-matchy can be ridiculously cute, but it is definitively NOT the photography way to go. If you have two people wearing the exact same color and texture, guess what happens when they stand next to each other? Yep, everything blends together into an indistinguishable mass.
Instead of matching, think of coordinating colors from similar color families. The overall look results in a more cohesive image with each person retaining their individual shape.
4. New England Style
When I first moved to Massachusetts, I was struck by an interesting New England phenomena: when the weather gets cold the sweaters and scarves come out to play. For those born here, this fashion tidbit might be obvious to you; however, in my New Jersey childhood we put on “jackets” and didn’t really do the whole scarf thing. It took me a while to accept this cultural difference; however, I’m going to totally come out and embrace this New England trend (along with the knee high boots) because sweaters and scarves are WAY more flattering than jackets for a photography session.
Coats and bulky jackets tend to distort a person’s shape, whereas a well fitting sweater or the addition of a coordinating cardigan can add interest to an outfit while flattering the figure. Scarves are also a great way to make for a quick “outfit” change to allow for some variety in your images.
5. You Do You

If you aren’t comfortable in the clothes you are wearing, you won’t look comfortable in your images.
Do you see this adorable couple? Apparently, there are “rules” about not wearing graphic-Ts for portraits, and only wearing classic blouses, dresses and/or some other nonsense. This couple sent me photo after photo of potential outfit choices in which they clearly looked miserable. Dresses and formal wear just weren’t their thing. They just didn’t feel like their authentic selves, so I worked with them to help them coordinate the clothes they would normally wear to create these portraits.
I’m a lifestyle photographer. This means that my photos aim to tell the stories of your lives. If you aren’t into dresses and you wear a dress, it’s not your story. I want you to look like your best self, but your true self.
Questions? Book a session today, and we’ll find an outfit that works for you.